


Earning His Keep

by emani-writes (Thrsdynxt)



Series: SPN Poly BINGO 2017 [1]
Category: Supernatural
Genre: Alternate Universe - Pirate, Anal Fingering, Dean (and others) hit Cas, Dirty Talk, Dubious Consent, Face Slapping, Face-Fucking, Implied/Referenced Rape/Non-con, M/M, Mildly Dubious Consent, Money Shot, Multi, Oral Sex, Pirate!Benny, Restraints, Smut, Sub/Dom undertones, Threesome - M/M/M, he gets kinda roughed up, injured!Cas, more than once, pirate!dean, ropes, stowaway!cas
Language: English
Status: Completed
Published: 2017-01-19
Updated: 2017-01-19
Packaged: 2018-09-18 12:39:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9385577
Author URL: https://archiveofourown.org/users/Thrsdynxt/pseuds/emani-writes
Summary: Castiel is caught as a stowaway aboard Captain Dean’s ship. Dean and First Mate Benny come up with a creative solution to allow Castiel to earn his keep.





	

**Author's Note:**

> Written for SPN Poly BINGO 2017  
> Square filled: **Pirate AU**
> 
> Want more? Read my follow-up: [Bringing Up the Rear](http://archiveofourown.org/works/9461966). Yes. That really is the title.

They hadn’t been at sea for three days when they found him. A stowaway hidden among the casks of ale in the belly of the ship. Such a pretty boy. That’s what Lucifer and Rafael had said, two of the more unsavory lot of Captain Dean’s crew. They’d had him pinned, palming his lithe body and bloodying his lip, and quite nearly naked before the First Mate had come to his rescue. If you could call it a rescue, which Castiel was no longer sure it really was as the bear of a man lead him roughly past the leering eyes of the rest of the crew, no shirt and breeches unlaced. 

Castiel wrapped his long thin arms around his chest, but the bitter salty spray caused him to erupt in gooseflesh regardless. At least it helped to hide his tears, Castiel thought bitterly. 

Beside him, large fist like a steel band around his arm, First Mate Benny bellowed to the ogling crew. “Back to work, you sorry sops!” 

Castiel cringed even further into himself.

They stopped in front of the dark wood door leading to the Captain’s quarters. Benny hardly paused to rap his knuckles before swinging open the door and shoving Castiel in before him. The room was dimly lit and modestly appointed and Castiel found himself grateful for a reprieve from the harsh wind that could be heard howling at the door.

Captain Dean stood at a worn desk, staring intently down at a map. The man hardly threw a glance at the door, turning only when he caught sight of a battered and shivering Castiel. He turned fully, planting his leather clad hip against the scarred wood of the table, arms crossed over his chest. 

“Well, well, Benny.” His voice was rich with amusement and Castiel found himself glancing up quickly at his smirking form before casting his eyes to the floor. “What do we have here?”

Benny smirked at the captain. “Seems as though some of your men, Cap, found themselves a stowaway.” He glanced down to the trembling Castiel before slapping his ass roughly causing the smaller man to gasp. “Saved him from Lucifer and Rafael. They weren’t too pleased, mind.”

Pushing himself from the table, Dean strode slowly toward them, circling. The sharp clomp of his boots caused Castiel to squeeze his eyes shut, his guts turning to ice in his fear. He opened his eyes as the footfall stopped, staring down intently at shiney black books, even as a tear dripped from his nose and landed on the polished toe. Rough, calloused fingers suddenly grasped his chin, tilting his head up with force until Castiel found himself staring into hard green eyes. 

“What’s your name, boy?” The gruff voice caused Castiel to shiver.

“Ca-Castiel,” he ground out only to cry out when Benny’s hand cracked down on his ass causing his flesh to burn and sting even through the loose layers of his breeches. 

The big man growled into his ear. “That any way to address your Captain?”

Tears ran down Castiel’s cheeks, and he dropped his chin to his chest in shame. “S-sir! M-my name is Castiel, sir.” A sob bubbled up from his throat.

Dean studied him a long moment before stepping back over to his desk and kicking out a chair. “Tie him up and go fetch us some dinner. Boy looks half starved.”

Benny paused, studying the Captain for a long moment before before a wicked grin spread across his stubbled face. “Yes, sir, Captain,” he all but purred before shoving Castiel into the proffered chair and securing him with quick, sure knots.

Pulling out a chair himself, Dean dropped gracefully into it even as Benny swung the door shut behind him. Leaning forward, Dean rested his elbows on his knees and Castiel focused all his attention at the thick black tattooes covering the exposed forearms even as he fought to even out his breathing.

Silence hang heavy between them. Castiel risked flicking his eyes up, startling slightly when he locked onto intense green, before dropping them quickly back down. 

“Are you going to kill me?” Castiel whispered, breathe punching out of him in a rush.

Dean sniffed, sitting up to lean back in his chair. “Well, now, Castiel. That depends, don’t it?” 

Castiel shivered at the way Dean drug out his name, wrapping his lips around every syllable. 

Dean’s smirk quickly dropped into a sneer. “Just what do you think you’re doing on my ship?”

Castiel’s body tightened in fear and his strained to lean forward, pressing against the bonds that criss-crossed his chest. “Please,” he croaked, eyes wide and wet.

The slap was unexpected across the fine bones of his cheek and Castiel cried out at his face throbbed. Dean resumed his relaxed position, resting an ankle across his knee. 

“Try again.”

Castiel gasped, desperation straining. “I need… I needed a ship that could take me to Safe Haven.”

“And you just thought you could steal a ride in mine?” Venom dripped from every word and Castiel’s panic was all consuming. Sobs gasped out of his heaving chest. 

“I di-didn’t have gold. And-and-and I needed… I couldn’t,” Castiel croaked, shaking his head in desperation and pulling so tightly against his bonds that he was beginning to lose sensation in his fingers.

Dean stood from his chair only to kneel before the sniveling boy, studying him intently. Rough fingers brushed back shocks of black hair and Castiel blinked up at him, startled. Dean frowned, tipping his head to the side in contemplation even as he continued to trace the lines of Castiel’s face. 

He sighed heavily, shaking his head. “And what, boy, made you think you could steal from me like that?” Dean’s mouth pinched in distaste. “Do you even know who I am?”

Eyes blinking rapidly, Castiel risked a stiff nod. “You’re Captain Dean Winchester, the most wanted pirate in all the realm.”

A brief glimmer of hope bloomed in Castiel’s chest as a small smile ghosted over Dean’s features. He cried out in shock when Dean’s heavy hand connected once more with his cheek.

Dean stood, pacing in agitation. “And yet you still thought you could steal aboard my ship?” He growled low in his throat. “I ought to toss your mangy hide over the side and be done with you.”

“No!” Castiel yelled, eyes wide in panic as he struggled again in earnest. “No! Please, Captain, sir! I’ll do anything!” Castiel’s throat constricted and he fought to pull in breath. “Please.” Head hung, Castiel sobbed, not even fighting when Dean lifted his face once more. A thumb dragged over his spit covered bottom lip, smearing across his cheek.

“Anything, huh?” Dean stared down his nose at Castiel, thumb tracing teasing circles. 

It was at just that moment, the door to the cabin swung open, and Benny strode back in carrying a platter of food and two steins of ale. Dean smirked down at Castiel before leering at his First Mate.

“Hey, Benny, Cas here says he’ll be willing to do _anything_ to be kept from going overboard.”

Benny turned from setting down his haul, eyes alight and eyeing the way the Captain was still teasing Castiel’s full lower lip. Benny rubbed his hands on his breeches before stepping up behind the Captain and wrapping the man up in his strong arms.

“Did he now, cher?” Benny’s hands pressed flat against Dean’s chest and stomach. Cold blue eyes locked with Castiel’s as Benny oh so slowly bend his head down to kiss the pulse point of Dean’s neck causing the captain’s eyes to fluttered close as he sighed. 

Castiel stared at the two men, eyes wide, jaw falling open in surprise even as something other than fear coiled in his gut. 

Benny continued to stare at him, supporting the captain’s weight as the man leaned into his sturdy frame. A hand slide down Dean’s belly brushing across the front of his leather pants to cup him, squeezing slightly and earning a groan from Dean and a hitched gasp from Castiel. 

Benny’s smirk turned predatory. He made quick work unlacing Dean’s pants and pulling him from the confines, stroking his hand lazily as the captain writhed in his strong grip. Castiel watched it all, mesmerized, before darting a glance up to meet Benny’s gaze.

“Anything, chief?” Benny slid a finger through the precum beading at the head of Dean’s cock. He released his grip only to bring his hand to his lips, sucking at the flavor he found there. 

Castiel was panting against the ropes, fear and desire warring for dominance across his features. He nodded. “ _Please_.”

“Well, ain’t you polite. And so pretty,” Benny said, reaching his hand down again to stroke Dean’s straining cock. “Isn’t he pretty, Captain? Just look at those lips on him. Bet he could suck your cock so good.” 

“God damnit, Benny,” Dean choked out, reaching out a hand again to cup Castiel’s swollen cheek. “Want him.”

Benny grinned. “You hear that, chief? The Captain wants you. Maybe you’ll be useful on this voyage after all.”

Benny shuffled forward, effectively brushing Dean purpling flesh against the seam of Castiel’s lips.

“You gonna be a good boy, Castiel? You gonna suck the Captain’s cock?”

Eyes wide and fixed on Benny, Castiel nodded before slowly opening his mouth. Dean pressed forward his hips, sliding in and moaning at the warm, wet tongue. He reached down and grasped a dark tuft of hair at the crown of Castiel’s head before pulling back and slowly, deliberately, fucking Castiel’s face. 

The man below his choked and sputtered, gasping for air on each outward stroke. Benny stayed behind Dean, chest supporting Dean’s shoulders even as his hands guided Dean’s hips.

Hot, wet lips were pressed to Dean’s ear. “That’s right, Captain,” Benny rumbled, using his hands to increase Dean’s speed. “Use that pretty mouth. So fucking good. Bet you can’t wait to fuck that little mouth while I’m pounding into your tight ass.”

Dean was letting out breathy moans and grunts with each thrust. “Oh, god, Benny.” He reached his free hand back behind him, gripping onto Benny’s neck, fingers digging in hard. 

Chuckling darkly, Benny let a hand drift down the back of Dean’s pants, and pressed a thick fingers against his hole. Dean clenched, gasping.

“That’s right, cher. Come all over his face,” Benny commanded, finger breeching Dean’s hole even as Dean pulled back with a soft cry, painting Castiel’s face with thick stripes.

Castiel sat panting, trying to regain the breath he’d been denied and darting out his pink tongue to taste Dean’s release. Benny smirked.

It took several moments for Dean to regain his composure. He stepped away from Benny and Castiel, tucking himself back into his pants before turning. Castiel was watching him with guarded eyes while Benny was grinning and palming himself through his breeches.

Dean shot a glare at Benny before contemplating Castiel. “You prepared to pay your way, boy?”

Lip trembling, Castiel nodded. “Yes, sir.” His voice was raw and used from the treatment he’d just received.

Dean pounded him hard on the back. “Excellent! Benny, untie him. Cas, eat up and once he’s done, Benny, tie him to the bed and prep him.” Dean grinned wide. “We’ve got so much more planned for you, pretty boy.”

Dean leaned down, pressing his stubbled chin against Castiel’s ear. “Benny’s going to make you ache so good.”

Castiel whimpered, eyeing the big man with his arms across his barrel of a chest. Stepping forward, Benny took Dean’s place next to the boy, untying him with quick tugs to his knots. He grabbed Castiel’s wrists, rubbing across the ligature marks and forcing feeling back into his cold fingers.

“Don’t fret, darling,” Benny murmured, smiling warmly for the first time. “It’s going to be an enjoyable 3 months. Just you wait.”

**Author's Note:**

> Visit me on tumblr at [emani-writes](http://emani-writes.tumblr.com/)!


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